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PEPPSI‐Type Palladium–NHC Complexes: Synthesis, Characterization, and Catalytic Activity in the Direct C5‐Arylation of 2‐Substituted Thiophene Derivatives with Aryl Halides
Author(s) -
Kaloğlu Murat,
Özdemir İsmail,
Dorcet Vincent,
Bruneau Christian,
Doucet Henri
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201601452
Subject(s) - thiophene , aryl , palladium , chemistry , alkyl , halide , pyridine , catalysis , medicinal chemistry , polymer chemistry , organic chemistry
Six benzimidazolium salts, having two nitrogen atoms substituted by various alkyl groups, have been synthesized in high yields. The benzimidazolium salts readily converted into the corresponding PEPPSI‐type palladium–NHC complexes (PEPPSI = pyridine‐enhanced precatalyst preparation, stabilization, and initiation). The structures of all compounds have been characterized by 1 H NMR, 13 C NMR, and IR spectroscopy, as well as elemental analysis techniques, which support the proposed structures. The molecular structure of one complex has been determined by single‐crystal X‐ray diffraction. The catalytic activity of the PEPPSI‐type palladium–NHC complexes has been evaluated with respect to the direct C5‐arylation of 2‐substituted thiophene derivatives with various aryl halides. This arylation occurs efficiently and selectively at the C5‐position of 2‐substituted thiophene derivatives.